88

Chester, MD Homes for Sale

Section Image Section Image
  • /62

    $530,000

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - $10,000 Closing Cost Assistance Available - Turn Key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 936-3917

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • /57

    $499,000

    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    CHESTER RIVER WATERFRONT on the Eastern Shore! Nestled within the water-privileged resort-style community of Queen's Landing, along the scenic Chester River and Macum Creek off the Chesapeake Bay. Step into the light-filled foyer and head up the stairs to the main level, you will find this lovely 2 bedroom, 2.5 bath condominium is move in ready. Just bring your patio chairs, sit back and enjoy

    Agent Photo

    Lona Todd

    Taylor Properties

    (667) 291-8898

    34 Queen Anne Way, Chester, MD 21619
  • /2

    $479,000

    • 3 Beds
    • 2.5 Baths
    • 1,899 Sq Ft

    312 Blenny Ln, Chester, MD 21619

    You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER VIEW-End UNIT! Come enjoy island living in the Bayside Community. Offering POND views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout

    Judith Brown Samson Properties

    312 Blenny Ln, Chester, MD 21619
  • /10

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft

    108 Bodys Neck Rd, Chester, MD 21619

    Coming Soon in Bayside on Kent Island – Resort-Style Island Living with Unmatched Water Views!Discover the perfect blend of coastal charm and modern luxury in this rarely available, oversized end-unit townhome Perfectly positioned to capture unobstructed, sweeping water views, this meticulously updated 3-bedroom, 2.5-bath home offers a true resort-style experience in one of the Eastern Shore’s

    Bill Longest Realty Navigator

    108 Bodys Neck Rd, Chester, MD 21619
  • /74

    $549,000

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    24 D Queen Elizabeth Ct, Chester, MD 21619

    Welcome to 24D Queen Elizabeth Ct, a beautifully updated 2-bedroom waterfront condo with a spacious loft that easily serves as a third bedroom, office, or bonus space. Nestled in the highly desirable Queens Landing community, this home offers spectacular front and back water views — enjoy both peaceful sunrises and vibrant sunsets every day.Inside, the open-concept layout is flooded with natural

    The Williams Home Team JPAR Maryland Living

    24 D Queen Elizabeth Ct, Chester, MD 21619
  • /79

    $529,500

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    49 Queen Guinivere Way, Chester, MD 21619

    Welcome to Queens Landing, where resort-style living meets the comfort of home. This beautifully updated townhome offers 1,440 square feet of thoughtfully designed living space plus an open sunroom, adding approximately 160 additional square feet, creating a seamless and spacious floor plan ideal for everyday living and entertaining.Enjoy panoramic water views from every room - lake and fountain

    Julia Stevens Realty Navigator

    49 Queen Guinivere Way, Chester, MD 21619
  • /47

    $575,000

    • 5 Beds
    • 3 Baths
    • 3,500 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    Need more room? This expansive home is ready to welcome your whole family! With 5 bedrooms, 3 full bathrooms and a 4-car garage, there's plenty of space for everyone to spread out and enjoy their own privacy.You'll be delighted by a mix of formal and casual living spaces, including a bright formal living room, a cozy lower-level family room, and a huge screened porch that’s perfect for relaxing

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, Chester, MD 21619
  • /68

    $549,000

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    Wake up to shimmering Chester River views and let every day feel like a getaway!This beautifully maintained 2.5-level townhome offers 1,680 square feet of stylish and functional living space in the sought-after waterfront community of Queens Landing. The main level features a cozy living area with a gas fireplace, luxury vinyl plank flooring, and access to a private patio where peaceful morning

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • /22

    $579,000

    • 4 Beds
    • 2.5 Baths
    • 2,558 Sq Ft

    558 Cross Creek Ct, Chester, MD 21619

    Welcome to your future home located in the highly sought after Clayborne Woods neighborhood, on a large corner wooded lot. Property boasts over 2500 usable square footage. Enter into a 2 story foyer with all new LVT on the entire level. Huge dining, separate eat in kitchen, 1/2 bath, family room with fireplace. Plus an added wing for your imagination that over looks a private wooded lot.?

    Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
  • /36

    $715,000

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    242 Peregrine Dr, Chester, MD 21619

    Introducing the Simone – Where Modern Comfort Meets Farmhouse Charm. This 6 month old Simone offers the perfect blend of open-concept living and timeless Farmhouse style with 4 spacious bedrooms, 3 full baths, and a 2-car garage, this home is designed with both functionality and flair. Step inside to find stylish laminate flooring flowing through the foyer, hallways, home office, great room,

    Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
  • /43

    $624,900

    • 5 Beds
    • 2.5 Baths
    • 2,656 Sq Ft

    1614 Postal Rd, Chester, MD 21619

    OPEN HOUSE Saturday 5/31 from 10:30-12:30pm! Welcome to this Lovingly and Well-Maintained Colonial Style Home zoned Residential and Commercial! Looking for a Home based business? This one is it, as it offers a rare opportunity with incredible versatility with Town Center Zoning, making it perfect for a private residence, bed & breakfast, Airbnb, or the opportunity to live where you work.

    Pamela Ackermann-Doll RE/MAX Executive

    1614 Postal Rd, Chester, MD 21619
  • /45

    $649,400

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    154 Harrier Way, Chester, MD 21619

    *** WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND***The Donegal model is a spacious and airy 2 bedroom, 2 bath home boasting an expansive open floor plan with nearly 2000 square feet of luxurious living space on one level. This home features a lavish gourmet kitchen and dining area, a spacious and airy great room with gas fireplace, plus office or den. You decide! The centerpiece

    Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
  • /51

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,564 Sq Ft

    1771 Harbor Dr, Chester, MD 21619

    This beautifully crafted waterfront home boasts five spacious bedrooms and 2.5 baths, offering ample space for comfortable living. The expansive layout includes multiple living areas, ideal for both relaxation and entertainment. The sunroom, with its wall-to-wall sliding doors, provides stunning views of the water, while the family room features a cozy fireplace. A separate formal living room and

    Dee Dee McCracken Coldwell Banker Realty

    1771 Harbor Dr, Chester, MD 21619
  • /26

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 2,342 Sq Ft

    114 Addison Ct, Chester, MD 21619

    **REDUCED** "Shiny and new" might be the best way to describe the feel of this lovely 3 bedroom, 2-1/2 bath home in the terrific Claybourne Woods community. The "new" includes a brand new roof, kitchen cabinets, granite kitchen counters, kitchen sink and faucet, wood floors downstairs and main level carpeting. The rest of the home is move-in ready and was just professionally cleaned. The

    Scott Saunders Coldwell Banker Waterman Realty

    114 Addison Ct, Chester, MD 21619
  • /51

    $684,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    516 Warbler Way, Chester, MD 21619

    Charming Comfort & Elevated Style – Jenkins, Lot 602 | Move-In September 2025Welcome to the Jenkins, a thoughtfully designed 2-bedroom, 2-bath home with a 2-car garage and open layout ideal for modern living. This layout includes a versatile home office, a peaceful screened patio, and a stunning 2-story stone fireplace—the perfect focal point for the great room.The kitchen is equipped with

    Mary Anne Kowalewski KOVO Realty

    516 Warbler Way, Chester, MD 21619
  • /51

    $669,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    416 Warbler Way, Chester, MD 21619

    Easy Living with Stylish Touches – Jenkins, Lot 597 | Move-In August 2025Step into comfort and convenience with the Jenkins—a 2-bedroom, 2-bath home with a 2-car garage, offering a smart layout and refined finishes. Designed for relaxed living, this home features a dedicated home office and a screened patio—perfect for quiet mornings or entertaining guests.The open-concept kitchen shines with

    Mary Anne Kowalewski KOVO Realty

    416 Warbler Way, Chester, MD 21619
  • /39

    $639,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    524 Warbler Way, Chester, MD 21619

    Easy Living Meets Timeless Style – Bernstein II, Lot 604Available for settlement in Summer 2025, the Bernstein II is a beautifully designed 2-bedroom, 2-bath home offering low-maintenance, single-level living with thoughtful upgrades throughout.Step inside to find Luxury Vinyl Plank flooring flowing throughout the main living areas, creating a warm, cohesive space that’s both stylish and durable.

    Mary Anne Kowalewski KOVO Realty

    524 Warbler Way, Chester, MD 21619
  • /48

    $639,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    211 Switchgrass Way Unit 1532, Chester, MD 21619

    The Chester is an elegant home that effortlessly blends a spacious open floorplan with timeless Legacy design elements. With a projected settlement date in September 2025, it promises modern living with stylish finishes.This thoughtfully designed home includes two bedrooms and two and a half baths, offering ample space and comfort. The one-car garage adds convenience and practicality to

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1532, Chester, MD 21619
  • /26

    $679,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    211 Switchgrass Way, Chester, MD 21619

    Private home office for working or reading.Chef-worthy gourmet kitchen & spacious island perfect for meal prepping.Elegant dining area with convenient dry bar, perfect for entertaining.Open, airy great room with electric fireplace & tray ceiling.Serene owner's suite with crown moulding and balcony access.Glamorous owner's spa bath featuring split vanities.Relaxing

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /12

    $862,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos, Chester, MD 21619

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional

    K Hovnanian's Four Seasons

    Mykonos, Chester, MD 21619
  • /27

    $797,900 New Construction

    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    Kerr, Chester, MD 21619

    Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    K Hovnanian's Four Seasons

    Kerr, Chester, MD 21619
  • /25

    $649,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    Jenkins II, Chester, MD 21619

    Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split vanities. Convenient HovHall off garage for keeping home tidy.

    K Hovnanian's Four Seasons

    Jenkins II, Chester, MD 21619
  • /21

    $559,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    Severn, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K Hovnanian's Four Seasons

    Severn, Chester, MD 21619
  • /11

    $752,900 New Construction

    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly, Chester, MD 21619

    Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in closet. Convenient covered patio with screen patio option.

    K Hovnanian's Four Seasons

    Kelly, Chester, MD 21619
  • /10

    $730,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    Taylor, Chester, MD 21619

    Secluded bedroom 2 and bath off foyer for overnight guests.Stylish home office off foyer for working from home.Open & airy great room with adjacent dining area.Striking kitchen with island & tons of cabinet space.Luxurious primary suite with oversized walk-in closet.Palatial primary bath with roomy shower.Convenient 3-car tandem garage for additional storage.

    K Hovnanian's Four Seasons

    Taylor, Chester, MD 21619
  • /14

    $681,900 New Construction

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    Simone, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities. Versatile loft on second

    K Hovnanian's Four Seasons

    Simone, Chester, MD 21619
  • /12

    $616,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    Bernstein II, Chester, MD 21619

    Elegant foyer welcoming guests to your home. Convenient single-story living. Kitchen with spacious pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private primary suite with large walk-in closet and spa bath. Laundry room and HovHall with plenty of space to store and organize.

    K Hovnanian's Four Seasons

    Bernstein II, Chester, MD 21619
  • /34

    $671,400 New Construction

    • 4 Beds
    • 2.5 Baths

    1501 Norman Rd, Chester, MD 21619

    One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for the whole family to spread out. Your main level features a spacious family room and table space kitchen. Add a light-filled morning room off the rear or expand your space with plan extension. Upstairs, plans accommodate 4 nicely sized bedrooms, 2 full baths and large laundry

    George Bailey Keller Williams Flagship

    1501 Norman Rd, Chester, MD 21619
  • /32

    $560,000

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    190 Harrier Way Unit 11, Chester, MD 21619

    Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell!Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel appliances, custom

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • /47

    $439,900 Open Sat 10AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft

    2707 Cox Neck Rd, Chester, MD 21619

    Welcome to Harborview, a long established community on Maryland's eastern shore, home of some of the best seafood on the eastern seaboard! Come see everything that living on "The Shore" has to offer. Fantastic dining on the Kent Narrows, shopping at the outlets, the new pickleball courts in nearby Stevensville and Grasonville, the dog park and of course the new skate park! The Cross Island trail

    Samantha Hernandez Douglas Realty, LLC

    2707 Cox Neck Rd, Chester, MD 21619
  • /60

    $354,900

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    35 F Queen Anne Way, Chester, MD 21619

    Welcome to 35F Queen Anne Way in Queens Landing! This lakefront updated home offers 2 bedrooms and 2 full bathrooms. Updates include a spacious kitchen and both bathrooms. Wake up to lakefront views from the spacious primary bedroom and enjoy a cup of coffee or a glass of wine on the back patio or three season room while gazing over the lake. A stones throw away is the scenic Chester River

    Lawrence Doyle Long & Foster Real Estate, Inc.

    35 F Queen Anne Way, Chester, MD 21619
  • /30

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft

    413 Dominion Rd, Chester, MD 21619

    KENT ISLAND *Single Family Home * 3 bedrooms, 2 full bathrooms * Main level has a spacious eat in kitchen with french doors leading to the backyard deck, family room with lots of natural light and brand new full bathroom with newer LG front loading washer and dryer * There are 3 bedrooms and a full bathroom with tub/shower upstairs *Heat pump system with central AC* Many upgrades through out the

    Suzanne Hitt Coldwell Banker Waterman Realty

    413 Dominion Rd, Chester, MD 21619
  • /23

    $396,000

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1838 Sherman Dr, Chester, MD 21619

    Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming single-story rancher offers the perfect blend of comfort, charm, and convenience. Set on a spacious, fully fenced lot, this home provides a serene retreat with plenty of outdoor space to relax or entertain.Step inside to find a bright and inviting interior with tasteful neutral tones, modern finishes, and a

    Kara Shaffer Engel & Völkers Annapolis

    1838 Sherman Dr, Chester, MD 21619
  • /40

    $539,500

    • 3 Beds
    • 3.5 Baths
    • 2,131 Sq Ft

    112 Harbour Sound Dr, Chester, MD 21619

    Resort Living at it's best!! Available furnished or unfurnished. Enjoy stunning, unobstructed water views in the highly sought after community of Bayside! Many recent upgrades and improvements to this home include renovated bathrooms (2024) , New garage door, with fresh sealing floor paint (2023) New Kitchen cabinets (2022), New Double Oven (2022) , New Quartz Countertops (2022) New flooring

    Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
  • /26

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    28E Queen Mary Ct, Chester, MD 21619

    Welcome to 28E Queen Mary Court — one of the largest condos in the sought-after Queens Landing community, offering 1,660 square feet of thoughtfully designed living space. This spacious 3-bedroom, 2.5-bath home is ideally positioned to take in the best of the neighborhood, with serene lake views from one side and the vibrant energy of the tennis and pickleball courts on the other.Tucked away on

    Justin Disborough Samson Properties

    28E Queen Mary Ct, Chester, MD 21619
  • /33

    $439,000

    • 4 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    1809 Stevens Dr, Chester, MD 21619

    Best deal on Kent Island! Beautiful 4 Bedroom 2 1/2 bath Cape on over 1/2 acre in peaceful Harbor View. Airy and spacious, this terrific home boasts 2 Bedrooms plus Full bath on the Main level with all new hardwood flooring and separate light -filled and cozy living and dining spaces. The gorgeous just updated kitchen features fabulous quartz countertops, all modern stainless steel appliances,

    Greg Koch Taylor Properties

    1809 Stevens Dr, Chester, MD 21619
  • /8

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    326 Hanna Ct, Chester, MD 21619

    Don't miss this incredible opportunity to own a spacious 4-bedroom home in sought-after Clayborne Woods at an exceptional price! Picture yourself relaxing by the gas fireplace, enjoying outdoor fun in the fenced backyard, or working/playing in the flexible space featuring stylish French doors. This is a rare find and won't last long – schedule your private tour today before it's gone!

    Kevin Waterman Coldwell Banker Waterman Realty

    326 Hanna Ct, Chester, MD 21619
  • /31

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,795 Sq Ft

    307 Skipper Ln, Chester, MD 21619

    Welcome to Your Refreshing New Home with First-Floor Living! This beautifully updated residence offers the perfect blend of comfort and convenience with three spacious bedrooms and two full baths, all on the main level. The expansive primary suite features a private, fully updated bath for your relaxation. The gorgeous kitchen is a true standout, boasting quartz countertops, brand new stainless

    Dee Dee McCracken Coldwell Banker Realty

    307 Skipper Ln, Chester, MD 21619
  • /45

    $374,900

    • 2 Beds
    • 2.5 Baths
    • 1,747 Sq Ft

    208 Ringneck Ct, Chester, MD 21619

    208 Ringneck Court is a great home for the smart buyer! This three-level, 2 bedroom, 2 1/2 bathroom garage town-home, located in the coveted Bayside Condominium neighborhood, was updated within the past 3 years. As you enter the south-facing home, you'll notice that the floor plan is a bit different than others...the kitchen has been reconfigured to create an open concept design which is ideal

    Phyllis Endrich Long & Foster Real Estate, Inc.

    208 Ringneck Ct, Chester, MD 21619
  • /26

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft

    203 Anchor Ln, Chester, MD 21619

    Think you've seen this one before? WE INVITE YOU TO TAKE A 2nd LOOK!! Staged and re-freshed you'll wonder why you didn't scoop this one up earlier! This adorable rancher has the traditional 3 bedrooms and 2 baths and so much more including a large dining area, kitchen with breakfast bar that flows into a large living room anchored by a beautiful brick fireplace. PLUS a large addition offers a

    Tricia Wilson Wilson Realty & Staging LLC

    203 Anchor Ln, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 3

How to Buy a Home How to Finance a Home How to Sell a Home